Hydrochloric Acid → HCID 86733489, compound

HRID 1077232Notes

Reaction equation

HRID 1077232 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:21]C)[CH2:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@:4]2([C:24]#[CH:25])[OH:23])[CH3:2].Cl.O>CO>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([C@@H:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@:4]2([C:24]#[CH:25])[OH:23])=[CH:16][C:15](=[O:21])[CH2:14][CH2:13]4)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 8673348813-Ethyl-3-methoxy-17alpha-ethynyl-17-hydroxy-6-methylgona-2,5(10)-diene

Product 1

HCID 86733489HCID 86733489, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve dl-13-ethyl-3-methoxy-6-methyl-17α-ethynyl-17-hydroxygona-2,5(10)-diene (3.5 g) in methanol (90 ml) containing concentrated hydrochloric acid (6.0 ml) and water (4.0 ml). Stir the solution under nitrogen for one hour. Work up in the usual fashion. Chromatograph on Florex (150 g), then recrystallize from ether-hexane to obtain dl-13-ethyl-17α-ethynyl-17-hydroxy-6α-methylgon-4-en-3-one (0.60 g) m.p. 148°-151°; ultraviolet absorption peak at 240 mμ (ε15,300), infrared maxima (chloroform) at 2.55 μ, 3.05 μ, 6.01 μ.

Workup

  1. customChromatograph on Florex (150 g), then recrystallize from ether-hexane

Sources & evidence

ORD record
ord-c06716b43e694e269fb21e9af64b74b5
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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